Organic thin film and method for producing organic thin film, organic electroluminescent element, display device, lighting device, organic thin film solar cell, photoelectric conversion element, thin film transistor, coating composition and material for organic electroluminescent elements

Abstract

The present invention aims to provide an organic thin film that imparts an excellent electron injection property and an excellent electron transport property when it is used as an electron injection layer of an organic EL device. The present invention relates to an organic thin film, which is a single film containing a first material which is a hexahydropyrimidopyrimidine compound having a structure of the following formula (1) and a second material which transports electrons, or a laminate film including a film containing the first material and a film containing the second material,wherein R1 is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4.

1 . An organic thin film, which is
 a single film containing a first material which is a hexahydropyrimidopyrimidine compound having a structure of the following formula (1) and a second material which transports electrons or   a laminate film including a film containing the first material and a film containing the second material,   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         2 . The organic thin film according to  claim 1 ,
 wherein the first material is a hexahydropyrimidopyrimidine compound of the formula (1) in which n is 2 or 3.   
     
     
         3 . A laminate film comprising:
 an oxide layer; and   a layer of the organic thin film according to  claim 1  formed on the oxide layer.   
     
     
         4 . An organic electroluminescence device comprising:
 a cathode;   an anode;   an emitting layer between the cathode and the anode; and   at least one selected from the group consisting of the organic thin film according to  claim 1  and a laminate film between the cathode and the emitting layer.   
     
     
         5 . The organic electroluminescence device according to  claim 4 , further comprising:
 an inorganic oxide layer between the cathode and the organic thin film.   
     
     
         6 . The organic electroluminescence device according to  claim 4 , comprising:
 a laminate film including the film containing the first material and the second material and the film containing the second material between the cathode and the emitting layer.   
     
     
         7 . The organic electroluminescence device according to  claim 6 ,
 wherein the layer containing the second material is present between the emitting layer and the film containing the first material and the second material.   
     
     
         8 . The organic electroluminescence device according to  claim 6 ,
 wherein the layer containing the second material is present between the cathode and the film containing the first material and the second material.   
     
     
         9 . The organic electroluminescence device according to  claim 4 ,
 wherein the layer containing the second material is present between the anode and the emitting layer.   
     
     
         10 . The organic electroluminescence device according to  claim 4 ,
 wherein the emitting layer contains the second material.   
     
     
         11 . An organic electroluminescence device material, comprising:
 a hexahydropyrimidopyrimidine compound having a structure of the following formula (1):   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         12 . An organic electroluminescence device comprising:
 a cathode;   an anode;   an emitting layer between the cathode and the anode; and   a layer containing the organic electroluminescence device material according to  claim 11  between the cathode and the anode.   
     
     
         13 . An organic electroluminescence device comprising:
 a cathode;   an anode;   an emitting layer between the cathode and the anode; and   a layer containing the organic electroluminescence device material according to  claim 11  between the cathode and the anode   wherein the layer containing the organic electroluminescence device material is present between the cathode and the emitting layer.   
     
     
         14 . An organic electroluminescence device comprising:
 a cathode;   an anode;   an emitting layer between the cathode and the anode;   a layer containing the organic electroluminescence device material according to  claim 11  between the cathode and the anode; and   an inorganic oxide layer between the cathode and the layer containing the organic electroluminescence device material according to  claim 11 .   
     
     
         15 . A display device, comprising:
 the organic electroluminescence device according to  claim 4 .   
     
     
         16 . A lighting system, comprising:
 the organic electroluminescence device according to  claim 4 .   
     
     
         17 . An organic thin film solar cell material, comprising:
 a hexahydropyrimidopyrimidine compound having a structure of the following formula (1):   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         18 . An organic thin film solar cell, comprising:
 the organic thin film according to  claim 1 .   
     
     
         19 . A photoelectric transducer material, comprising:
 a hexahydropyrimidopyrimidine compound having a structure of the following formula (1):   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         20 . A photoelectric transducer, comprising:
 the organic thin film according to  claim 1 .   
     
     
         21 . A thin film transistor material, comprising:
 a hexahydropyrimidopyrimidine compound having a structure of the following formula (1):   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         22 . A thin film transistor, comprising:
 the organic thin film according to  claim 1 .   
     
     
         23 . A coating composition, comprising:
 a first material which is a hexahydropyrimidopyrimidine compound having a structure of the following formula (1); and   a second material which transports electrons,   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         24 . A coating composition, comprising:
 a hexahydropyrimidopyrimidine compound having a structure of the following formula (1),   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         25 . A method for producing an organic thin film, comprising:
 forming a single film containing a first material which is a hexahydropyrimidopyrimidine compound having a structure of the following formula (1) and a second material which transports electrons on a surface on which the organic thin film is to be formed; or   forming successively a film containing the first material and a film containing the second material on the surface on which the organic thin film is to be formed,   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         26 . A method for producing an organic thin film, comprising:
 forming a film containing a hexahydropyrimidopyrimidine compound having a structure of the following formula (1) on a surface on which the organic thin film is to be formed,   
       
         
           
           
               
               
           
         
       
       wherein R 1  is an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, an optionally substituted arylalkylene group, an optionally substituted divalent to tetravalent acyclic or cyclic hydrocarbon group, a group of a combination of two or more of these groups, or a group of a combination of one or more of these groups and a nitrogen atom; and n is an integer of 1 to 4. 
     
     
         27 . The method for producing an organic thin film according to  claim 26 ,
 wherein the surface on which the organic thin film is to be formed contains a second material.